Glycinamide hydrochloride → HCID 11324179, compound

HRID 2254682Notes

Reaction equation

HRID 2254682 reaction equation
[ClH:1].[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].[C:7]([BH3-])#N.[Na+].Cl[C:12]1[C:13]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:14]([CH:17]=[CH:18][CH:19]=1)C=O>CO>[Cl:1][C:26]1[CH:27]=[C:22]([CH:23]=[CH:24][CH:25]=1)[CH2:21][O:20][C:13]1[CH:12]=[CH:19][C:18]([CH2:7][NH:2][CH2:3][C:4]([NH2:6])=[O:5])=[CH:17][CH:14]=1

Participants

5

Reactant 3

HCID 2723639Glycinamide hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 54026983HCID 54026983, compound

Product 1

HCID 11324179HCID 11324179, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

22.4 g (0.203 mol) of glycinamide hydrochloride are suspended in 1000 ml of dry methanol and 10.2 g (0.162 mol) of sodium cyanoborohydride are added while stirring under nitrogen. After solubilization of the mixture, 50 g (0.203 mol) of 3-chlorobenzyloxybenzaldehyde are added in a single portion. The reaction mixture is stirred 8 hours at room temperature and then allowed to stand 16 hours. The solution is filtered and evaporated, taken up with water and extracted three times with methylene chloride. After drying and evaporating, the crude residue is chromatographed on silica gel (eluant: chloroform/methanol/conc. NH4OH; 97/3/0.3) to give 2-[4-(3-chlorobenzyl)oxybenzyl] aminoacetamide which by reaction with the stoichiometric amount of gaseous HCl in ethanol is transformed into its hydrochloride (32.1 g, 46.3%, m.p.: 225°-230° C.).

Workup

  1. stirringThe reaction mixture is stirred 8 hours at room temperature
  2. filtrationThe solution is filtered
  3. customevaporated
  4. extractionextracted three times with methylene chloride
  5. customAfter drying
  6. customevaporating
  7. customthe crude residue is chromatographed on silica gel (eluant: chloroform/methanol/conc. NH4OH; 97/3/0.3)

Sources & evidence

ORD record
ord-b2815b51599b425ebb4536ee1092c36c
Source dataset
uspto-grants-1993_08
Patent number
US05236957

Reaction notes

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